CA1041556A - Methode d'isomerisation des olefines - Google Patents

Methode d'isomerisation des olefines

Info

Publication number: CA1041556A
Authority: CA; Canada
Prior art keywords: olefin; olefins; catalyst; vinylidene; carbon atoms
Prior art date: 1974-07-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA229,721A

Other languages

English (en)

Other versions

CA229721S (en

Inventor

Werner Strassberger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-07-06

Filing date

1975-06-19

Publication date

1978-10-31

1974-07-06 Priority claimed from DE19742432586 external-priority patent/DE2432586C2/de

1975-06-19 Application filed by Hoechst AG filed Critical Hoechst AG

1978-10-31 Application granted granted Critical

1978-10-31 Publication of CA1041556A publication Critical patent/CA1041556A/fr

Status Expired legal-status Critical Current

Links

150000001336 alkenes Chemical class 0.000 title claims abstract description 41
238000000034 method Methods 0.000 title claims abstract description 14
239000003054 catalyst Substances 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims abstract description 11
238000006317 isomerization reaction Methods 0.000 claims abstract description 11
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 8
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 6
239000008262 pumice Substances 0.000 claims abstract description 4
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims abstract description 3
239000004408 titanium dioxide Substances 0.000 claims abstract description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 18
239000000454 talc Substances 0.000 claims description 5
229910052623 talc Inorganic materials 0.000 claims description 5
238000004061 bleaching Methods 0.000 claims description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 3
229910052622 kaolinite Inorganic materials 0.000 claims description 3
229910052901 montmorillonite Inorganic materials 0.000 claims description 3
229910052898 antigorite Inorganic materials 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
229910052903 pyrophyllite Inorganic materials 0.000 claims description 2
150000004760 silicates Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 5
-1 vinylidene olefins Chemical class 0.000 abstract description 2
150000001735 carboxylic acids Chemical class 0.000 abstract 1
150000002118 epoxides Chemical class 0.000 abstract 1
150000003460 sulfonic acids Chemical class 0.000 abstract 1
229920002554 vinyl polymer Polymers 0.000 description 8
239000000047 product Substances 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
210000002741 palatine tonsil Anatomy 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
239000010936 titanium Substances 0.000 description 2
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2512—Catalytic processes with metal oxides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA229,721A 1974-07-06 1975-06-19 Methode d'isomerisation des olefines Expired CA1041556A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742432586 DE2432586C2 (de)		1974-07-06	Verfahren zur Herstellung von Olefinen durch Isomerisierung

Publications (1)

Publication Number	Publication Date
CA1041556A true CA1041556A (fr)	1978-10-31

Family

ID=5919913

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA229,721A Expired CA1041556A (fr)	1974-07-06	1975-06-19	Methode d'isomerisation des olefines

Country Status (8)

Country	Link
US (1)	US3940452A (fr)
JP (1)	JPS5134102A (fr)
BE (1)	BE831087A (fr)
CA (1)	CA1041556A (fr)
FR (1)	FR2277057A1 (fr)
GB (1)	GB1460684A (fr)
IT (1)	IT1039713B (fr)
NL (1)	NL7507808A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4697040A (en) *	1986-02-25	1987-09-29	Chevron Research Company	Isomerization of vinylidene olefins
JP4807519B2 (ja) *	2007-02-22	2011-11-02	マツダ株式会社	焼結鍛造部材の製造方法
US9266793B2 (en)	2012-12-26	2016-02-23	Chevron Phillips Chemical Company Lp	Acid-catalyzed olefin oligomerizations
US20140275664A1 (en)	2013-03-13	2014-09-18	Chevron Phillips Chemical Company Lp	Processes for Preparing Low Viscosity Lubricants
US9708549B2 (en)	2013-12-18	2017-07-18	Chevron Phillips Chemical Company Lp	Method for making polyalphaolefins using aluminum halide catalyzed oligomerization of olefins

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB549139A (en) *	1940-01-16	1942-11-09	Standard Oil Dev Co	Catalytic isomerization
US2603591A (en) *	1950-02-11	1952-07-15	Socony Vacuum Oil Co Inc	Pulsating hydrocarbon conversion
US3448164A (en) *	1967-09-21	1969-06-03	Phillips Petroleum Co	Olefin skeletal isomerization and catalyst

1974
- 1974-08-15 US US05/497,943 patent/US3940452A/en not_active Expired - Lifetime
1975
- 1975-06-19 CA CA229,721A patent/CA1041556A/fr not_active Expired
- 1975-07-01 NL NL7507808A patent/NL7507808A/xx unknown
- 1975-07-04 GB GB2825175A patent/GB1460684A/en not_active Expired
- 1975-07-04 JP JP50082029A patent/JPS5134102A/ja active Pending
- 1975-07-04 IT IT25132/75A patent/IT1039713B/it active
- 1975-07-07 BE BE158057A patent/BE831087A/fr unknown
- 1975-07-07 FR FR7521215A patent/FR2277057A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
DE2432586B1 (de)	1975-12-04
BE831087A (fr)	1976-01-07
US3940452A (en)	1976-02-24
FR2277057A1 (fr)	1976-01-30
DE2432586A1 (fr)	1975-12-04
IT1039713B (it)	1979-12-10
JPS5134102A (en)	1976-03-23
GB1460684A (en)	1977-01-06
NL7507808A (nl)	1976-01-08

Publication	Publication Date	Title
US4101600A (en)	1978-07-18	Method of dimerization of alpha-olefins
US5089458A (en)	1992-02-18	Synthetic saponite-derivatives, a method for preparing such saponites and their use in catalytic (hydro) conversions
US3352938A (en)	1967-11-14	Olefin double-bond isomerization using a mixture of platinum group metals as a catalyst
US4628138A (en)	1986-12-09	Catalyst and process for oligomerization of ethylene
AU677186B2 (en)	1997-04-17	Multi-stage olefin isomerization
US4289919A (en)	1981-09-15	Catalytic isomerization of an internal double bond aliphatic mono-olefin to produce terminal bond olefin
US3463827A (en)	1969-08-26	Novel metal carbonyl catalysts and their use
US2361613A (en)	1944-10-31	Isomerization of hydrocarbons
US3940452A (en)	1976-02-24	Isomerization of C10 -C70 olefins of vinylidene structure to olefins of vinyl structure
US5166114A (en)	1992-11-24	Ethylene dimerization and catalyst therefor
US5260499A (en)	1993-11-09	Ethylene dimerization and catalyst therefor
JPS63284137A (ja)	1988-11-21	ブタジエンおよび硫黄化合物を含むｃ４炭化水素留分における１−ブテンの２−ブテンへの異性化方法
JPH04211618A (ja)	1992-08-03	トルエンとブタジエンをスチレンと１−ペンテンに転化する方法
US3113166A (en)	1963-12-03	Polymerization of ethylene in the presence of a nickel oxide catalyst
US4272406A (en)	1981-06-09	Refractory metal oxide/silica supported nickel cluster catalyst
US5073658A (en)	1991-12-17	Catalyst comprising TiO2 dispersed phase on a monolayer of SiO2 on alumina support
US4628139A (en)	1986-12-09	Bis(1,5-cyclooctadiene)Ni(O) catalyst and process for oligomerization of ethylene
US4692430A (en)	1987-09-08	Zinc aluminate double bond isomerization catalyst and process for its production
US3280212A (en)	1966-10-18	Conversion of hydrocarbons
US5321193A (en)	1994-06-14	Skeletal isomerication of olefins with an alumina based catalyst
RU2368419C2 (ru)	2009-09-27	Улучшенный сокатализатор для производства линейных альфа-олефинов
US3880938A (en)	1975-04-29	Hydroformylation using aged zeolite-alumina hydrosol dispersion
US3395196A (en)	1968-07-30	Olefin disproportinoation
SU681034A1 (ru)	1979-08-25	Способ получени -олефинов
GB2076685A (en)	1981-12-09	Metal modified refractory metal oxide/silica supported nickel cluster catalyst